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- Nachgewiesen in: USPTO Patent Applications
- Sprachen: English
- Document Number: 20120003298
- Publication Date: January 5, 2012
- Appl. No: 13/097850
- Application Filed: April 29, 2011
- Claim: 1. A method for inducing an immune response in a subject, comprising administering to the subject a compound having a structure according to Formula A or Formula B: [chemical expression included] or a pharmaceutically acceptable salt, tautomer or hydrate thereof, wherein: X1 is —O—, —S—, or —NRa—; Ra is hydrogen, C1-C10 alkyl, or substituted C1-C10 alkyl, or Ra and R1 taken together with the nitrogen atom can form a heterocyclic ring or a substituted heterocyclic ring, wherein the substituents on the alkyl or heterocyclic groups are hydroxy, C1-C10 alkyl, hydroxyl C1-C10 alkenyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C1-C6 alkoxy C1-C6 alkylene, amino, cyano, halogen or aryl; R1 is hydrogen, C1-C10 alkyl, substituted C1-C10 alkyl, C1-C10 alkoxy, substituted C1-C10 alkoxy, C3-C9 cycloalkyl, substituted C3-C9 cycloalkyl, C5-C10 aryl, substituted C5-C10 aryl, C5-C9 heterocyclic, substituted C5-C9 heterocyclic, C1-C6 alkanoyl, Het, Het C1-C6 alkyl, or C1-C6 alkoxycarbonyl, wherein the substituents on the alkyl, cycloalkyl, alkanoyl, alkcoxycarbonyl, Het, aryl or heterocyclic groups are hydroxyl, C1-C10 alkyl, hydroxyl C1-C10 alkylene, C1-C6 alkoxy, C3-C9 cycloalkyl, C5-C9 heterocyclic, C1-6 alkoxy C1-6 alkenyl, amino, cyano, halogen or aryl; each R2 independently is hydrogen, —OH, C1-C6 alkyl, substituted C1-C6 alkyl, C1-C6 alkoxy, substituted C1-C6 alkoxy, —C(O)—C1-C6 alkyl (alkanoyl), substituted —C(O)—C1-C6 alkyl, —C(O)—C6-C10 aryl (aroyl), substituted —C(O)—C6-C10 aryl, —C(O)OH (carboxyl), —C(O)O—C1-C6 alkyl (alkoxycarbonyl), substituted —C(O)O—C1-C6 alkyl, —NRaRb, —C(O)NRbRc (carbamoyl), substituted C(O)NRbRc, C5-C9 cyclic, substituted C5-C9 cyclic, C5-C9 heterocyclic, substituted C5-C9 heterocyclic, halo, nitro, or cyano, wherein the substituents on the alkyl, cyclic, aryl or heterocyclic groups are hydroxy, C1-C10 alkyl, hydroxyl C1-C10 alkylene, C1-C6 alkoxy, C3-C6 cycloalkyl, C1-C6 alkoxy C1-C6 alkylene, amino, cyano, halogen or aryl; each Rb and Rc independently is hydrogen, C1-C10 alkyl, substituted C1-C10 alkyl, C1-C10 alkoxy, substituted C1-C10 alkoxy, C3-C9 cycloalkyl, substituted C3-C9 cycloalkyl, C5-C10 aryl, substituted C5-C10 aryl, C5-C9 heterocyclic, substituted C5-C9 heterocyclic, C1-C6 alkanoyl, Het, Het C1-C6 alkyl, or C1-C6 alkoxycarbonyl, wherein the substituents on the alkyl, cycloalkyl, alkanoyl, alkcoxycarbonyl, Het, aryl or heterocyclic groups are hydroxyl, C1-C10 alkyl, hydroxyl C1-C10 alkylene, C1-C6 alkoxy, C3-C9 cycloalkyl, C5-C9 heterocyclic, C1-6 alkoxy C1-6 alkenyl, amino, cyano, halogen or aryl; X2 is a bond or a linking group; n is 0, 1, 2, 3 or 4; and X3 is —PO4—; R3 is a C1-C6 alkyl substituted with —OC(O)—Rd and —OC(O)—Re; C1-C6 alkyl substituted with —OC(O)—Rd, —OC(O)—Re, and one or more further substituents; C1-C6 alkenyl substituted with —OC(O)—Rd and —OC(O)—Re; or C1-C6 alkenyl substituted with —OC(O)—Rd, —OC(O)—Re, and one or more further substituents; wherein the one or more further substituents independently are hydroxyl, C1-C10 alkyl, hydroxyl C1-C10 alkylene, C1-C6 alkoxy, C3-C9 cycloalkyl, C5-C9 heterocyclic, C1-6 alkoxy C1-6 alkylene, amino, cyano, halogen or aryl; each Rd and Re independently is a linear and saturated C6-C30 alkyl.
- Claim: 2. The method of claim 1, which comprises administering an antigen to the subject.
- Claim: 3. The method of claim 1, wherein Rd and Re independently are a linear and saturated C8-C18 alkyl.
- Claim: 4. The method of claim 1, wherein Rd and Re independently are a linear and saturated C8, C12 or C18 alkyl.
- Claim: 5. The method of claim 1, wherein Rd and Re are the same.
- Claim: 6. The method of claim 1, wherein —X2—X3—R3 taken together form a structure according to Formula C: [chemical expression included]
- Claim: 7. The method of claim 1, wherein X1 is O.
- Claim: 8. The method of claim 1, wherein R1 is a C1-C10 alkyl substituted with C1-6 alkoxy.
- Claim: 9. The method of claim 1, wherein n is 0 and X2 is —C(O)NH—(CH2)2—.
- Claim: 10. The method of claim 1, wherein R3 is a C3 alkyl substituted with —OC(O)—Rd and —OC(O)—Re.
- Claim: 11. The method of claim 10, wherein the R3C3 alkyl is substituted with —OC(O)—Rd at position 3 and —OC(O)—Re at position 2 of the C3 alkyl.
- Claim: 12. The method of claim 1, wherein Rd and Re are a saturated and linear C1-2 alkyl.
- Claim: 13. The method of claim 1, wherein X1 is O, R1 is —(CH2)2—OCH3, n is 0, X2 is —C(O)NH—(CH2)2—, X3 is phosphate, R3 is a C3 alkyl substituted with —OC(O)—Rd and —OC(O)—Re, and Rd and Re are a linear and saturated C12 alkyl.
- Claim: 14. The method of claim 1, wherein the compound is SC12.
- Claim: 15. The method of claim 2, wherein the antigen and the compound are in one composition.
- Claim: 16. The method of claim 2, wherein the antigen and the compound are in different compositions.
- Claim: 17. The method of claim 1, wherein the compound has an adjuvant activity.
- Claim: 18. The method of claim 1, wherein the compound is in association with a liposome.
- Claim: 19. The method of claim 1, wherein the immune response is an antibody response.
- Claim: 20. The method of claim 19, wherein the antibody response is a IgG1a or IgG2a antibody response.
- Claim: 21. The method of claim 2, wherein the antigen is a microbial antigen.
- Claim: 22. The method of claim 1, wherein the compound is administered to the bladder.
- Claim: 23. The method of claim 22, wherein the compound is administered by intravesical instillation into the bladder.
- Claim: 25. The method of claim 1, wherein the compound is administered to the skin.
- Claim: 26. The method of claim 25, wherein the compound is administered by topical delivery to the skin.
- Current U.S. Class: 424/450
- Current International Class: 61; 61; 61
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